(S)-2-amino-4,5,6,7-tetrahydro-5-oxo-4-phenyl-cyclopenta[b]pyran-3-carbonitrile | 1311961-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (S)-2-amino-4,5,6,7-tetrahydro-5-oxo-4-phenyl-cyclopenta[b]pyran-3-carbonitrile
• 英文别名: (4S)-2-amino-5-oxo-4-phenyl-6,7-dihydro-4H-cyclopenta[b]pyran-3-carbonitrile
• CAS: 1311961-47-3
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: BOYNUDBABDDQKP-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-环戊二酮 、 苄烯丙二腈 在 3-[[[3,5-双（三氟甲基）苯基]氨基]-4-[[（（8α，9S）-6''-甲氧基七氢呋喃-9-基]氨基]-3-环丁烯-1,2-二酮 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以32%的产率得到
  参考文献：
  名称：

  Enantioselective synthesis of 2-amino-5,6,7,8-tetrahydro-5-oxo-4H-chromene-3-carbonitriles using squaramide as the catalyst

  摘要：

  The organocatalyzed enantioselective synthesis of a series of chiral 2-amino-5,6,7,8-tetrahydro-5-oxo-4H-chromene-3-carbonitriles was achieved using bifunctional squaramides as the catalysts. The tandem Michael addition-cyclization reaction of cyclohexane-1,3-diones and benzylidenemalononitriles gave the corresponding products in excellent yields (up to 99%) and moderate to good enantioselectivities (up to 83% ee). This investigation provides an efficient and useful process for the synthesis of chiral 2-amino-4H-chromenes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.09.011

文献信息

• Enantioselective synthesis of 2-amino-5,6,7,8-tetrahydro-5-oxo-4H-chromene-3-carbonitriles using squaramide as the catalyst
  作者：Yu Gao、Da-Ming Du

  DOI：10.1016/j.tetasy.2012.09.011

  日期：2012.10

  The organocatalyzed enantioselective synthesis of a series of chiral 2-amino-5,6,7,8-tetrahydro-5-oxo-4H-chromene-3-carbonitriles was achieved using bifunctional squaramides as the catalysts. The tandem Michael addition-cyclization reaction of cyclohexane-1,3-diones and benzylidenemalononitriles gave the corresponding products in excellent yields (up to 99%) and moderate to good enantioselectivities (up to 83% ee). This investigation provides an efficient and useful process for the synthesis of chiral 2-amino-4H-chromenes. (C) 2012 Elsevier Ltd. All rights reserved.